Asymmetric Synthesis of cis-3,4-Disubstituted Chromans and Dihydrocoumarins via an Organocatalytic Michael Addition/ Hemiacetalization Reaction
The organocatalytic domino Michael/hemiacetalization reaction between various aldehydes and ortho‐nitrovinylphenols has been developed. Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis‐3,4‐disubstituted chromanols are obtained in high to excellent yields (81–98%) and stereoselectiv...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2010-11, Vol.352 (17), p.2869-2874 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Enders, Dieter Wang, Chuan Yang, Xuena Raabe, Gerhard |
| description | The organocatalytic domino Michael/hemiacetalization reaction between various aldehydes and ortho‐nitrovinylphenols has been developed. Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis‐3,4‐disubstituted chromanols are obtained in high to excellent yields (81–98%) and stereoselectivities (dr: 86:14 to >99:1, ee 96 to >99%). The corresponding disubstituted chromans are available by dehydroxylation of the domino products in good to excellent yields (58–95%). Furthermore, oxidation of the domino products with pyridinium chlorochromate provided 3,4‐dihydrocoumarins in good yields (65–83%) without any epimerization. |
| doi_str_mv | 10.1002/adsc.201000659 |
| format | Article |
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Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis‐3,4‐disubstituted chromanols are obtained in high to excellent yields (81–98%) and stereoselectivities (dr: 86:14 to >99:1, ee 96 to >99%). The corresponding disubstituted chromans are available by dehydroxylation of the domino products in good to excellent yields (58–95%). Furthermore, oxidation of the domino products with pyridinium chlorochromate provided 3,4‐dihydrocoumarins in good yields (65–83%) without any epimerization.</description><identifier>ISSN: 1615-4150</identifier><identifier>ISSN: 1615-4169</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201000659</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>3,4‐dihydrocoumarins ; 4-dihydrocoumarins ; Aldehydes ; Asymmetry ; Catalysis ; chromans ; Ethers ; hemiacetalization ; Michael addition ; Michael reaction ; organocatalysis ; Oxidation ; Pyridinium chlorochromate ; Stereoselectivity ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2010-11, Vol.352 (17), p.2869-2874</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4599-edc4999937a3c67bcdc1a09ceb56e69165a9511f187feac0447b5e44344780933</citedby><cites>FETCH-LOGICAL-c4599-edc4999937a3c67bcdc1a09ceb56e69165a9511f187feac0447b5e44344780933</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.201000659$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201000659$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27931,27932,45581,45582</link.rule.ids></links><search><creatorcontrib>Enders, Dieter</creatorcontrib><creatorcontrib>Wang, Chuan</creatorcontrib><creatorcontrib>Yang, Xuena</creatorcontrib><creatorcontrib>Raabe, Gerhard</creatorcontrib><title>Asymmetric Synthesis of cis-3,4-Disubstituted Chromans and Dihydrocoumarins via an Organocatalytic Michael Addition/ Hemiacetalization Reaction</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>The organocatalytic domino Michael/hemiacetalization reaction between various aldehydes and ortho‐nitrovinylphenols has been developed. Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis‐3,4‐disubstituted chromanols are obtained in high to excellent yields (81–98%) and stereoselectivities (dr: 86:14 to >99:1, ee 96 to >99%). The corresponding disubstituted chromans are available by dehydroxylation of the domino products in good to excellent yields (58–95%). Furthermore, oxidation of the domino products with pyridinium chlorochromate provided 3,4‐dihydrocoumarins in good yields (65–83%) without any epimerization.</description><subject>3,4‐dihydrocoumarins</subject><subject>4-dihydrocoumarins</subject><subject>Aldehydes</subject><subject>Asymmetry</subject><subject>Catalysis</subject><subject>chromans</subject><subject>Ethers</subject><subject>hemiacetalization</subject><subject>Michael addition</subject><subject>Michael reaction</subject><subject>organocatalysis</subject><subject>Oxidation</subject><subject>Pyridinium chlorochromate</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>1615-4150</issn><issn>1615-4169</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkU9vEzEQxVcIJErhytlHDmxqr9d2fIwSaJCaVmrLn5s18c4Sw-66tb3A8iX4yjhKFfXWuczT-Pfewa8o3jI6Y5RWZ9BEO6to1lQK_aw4YZKJsmZSPz9qQV8Wr2L8QSlTc6VOin-LOPU9puAsuZmGtMPoIvEtsS6W_H1drlwctzG5NCZsyHIXfA9DJDA0ZOV2UxO89WMPweXjLwf5gVyF7zB4Cwm6KeXcjbM7wI4smsYl54czssbegcUMuL-wP5FrBLsXr4sXLXQR3zzs0-Lzxw-3y3V5cXX-abm4KG0ttC6xsbXOwxVwK9XWNpYB1Ra3QqLUTArQgrGWzVWbk2ldq63AuuZZzKnm_LR4d8i9C_5-xJhM76LFroMB_RgNU5lkWnD1NEo5q7SkFcvo7IDa4GMM2Jq74PLnTBky-5LMviRzLCkb9MHw23U4PUGbxepm-dhbHrwuJvxz9EL4aaTiSpivl-dmI759EdXm1qz5f7ZTpxM</recordid><startdate>20101122</startdate><enddate>20101122</enddate><creator>Enders, Dieter</creator><creator>Wang, Chuan</creator><creator>Yang, Xuena</creator><creator>Raabe, Gerhard</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20101122</creationdate><title>Asymmetric Synthesis of cis-3,4-Disubstituted Chromans and Dihydrocoumarins via an Organocatalytic Michael Addition/ Hemiacetalization Reaction</title><author>Enders, Dieter ; Wang, Chuan ; Yang, Xuena ; Raabe, Gerhard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4599-edc4999937a3c67bcdc1a09ceb56e69165a9511f187feac0447b5e44344780933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>3,4‐dihydrocoumarins</topic><topic>4-dihydrocoumarins</topic><topic>Aldehydes</topic><topic>Asymmetry</topic><topic>Catalysis</topic><topic>chromans</topic><topic>Ethers</topic><topic>hemiacetalization</topic><topic>Michael addition</topic><topic>Michael reaction</topic><topic>organocatalysis</topic><topic>Oxidation</topic><topic>Pyridinium chlorochromate</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Enders, Dieter</creatorcontrib><creatorcontrib>Wang, Chuan</creatorcontrib><creatorcontrib>Yang, Xuena</creatorcontrib><creatorcontrib>Raabe, Gerhard</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Enders, Dieter</au><au>Wang, Chuan</au><au>Yang, Xuena</au><au>Raabe, Gerhard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Synthesis of cis-3,4-Disubstituted Chromans and Dihydrocoumarins via an Organocatalytic Michael Addition/ Hemiacetalization Reaction</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2010-11-22</date><risdate>2010</risdate><volume>352</volume><issue>17</issue><spage>2869</spage><epage>2874</epage><pages>2869-2874</pages><issn>1615-4150</issn><issn>1615-4169</issn><eissn>1615-4169</eissn><abstract>The organocatalytic domino Michael/hemiacetalization reaction between various aldehydes and ortho‐nitrovinylphenols has been developed. Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis‐3,4‐disubstituted chromanols are obtained in high to excellent yields (81–98%) and stereoselectivities (dr: 86:14 to >99:1, ee 96 to >99%). The corresponding disubstituted chromans are available by dehydroxylation of the domino products in good to excellent yields (58–95%). Furthermore, oxidation of the domino products with pyridinium chlorochromate provided 3,4‐dihydrocoumarins in good yields (65–83%) without any epimerization.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201000659</doi><tpages>6</tpages></addata></record> |
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| subjects | 3,4‐dihydrocoumarins 4-dihydrocoumarins Aldehydes Asymmetry Catalysis chromans Ethers hemiacetalization Michael addition Michael reaction organocatalysis Oxidation Pyridinium chlorochromate Stereoselectivity Synthesis |
| title | Asymmetric Synthesis of cis-3,4-Disubstituted Chromans and Dihydrocoumarins via an Organocatalytic Michael Addition/ Hemiacetalization Reaction |
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